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A common mistake students make during Hofmann elimination, aside from not choosing the correct β-carbon, is forgetting to form the quaternary ammonium salt before attempting the elimination step.
Here’s what happens:
Students sometimes jump straight into thinking it’s like an E2 reaction and try to eliminate directly from a regular amine (like a tertiary or secondary amine).
But Hofmann elimination requires converting the amine into a quaternary ammonium salt (usually using excess methyl iodide), followed by treatment with a strong base like silver oxide and water. Without this step, the elimination won't happen.
Other related mistakes include:
Using the wrong base — like hydroxide or an E2-style base instead of silver oxide and water.
Assuming Zaitsev product will form — Hofmann elimination is unique because it usually gives the least substituted (Hofmann) alkene, due to steric hindrance, not the most substituted like in E2 reactions.
Replied on Lesson: Oxidation Reactions of Alcohols
08 Apr 11:19
At this time we do not have any videos on this topic but I'll let the team know. For now here's information on these topics:
Oxone is the brand name for a triple salt:
2KHSO₅ · KHSO₄ · K₂SO₄
The key component here is potassium peroxymonosulfate (KHSO₅), a powerful oxidizing agent.
What is it used for?
Epoxidation of alkenes
Oxidation of sulfides to sulfoxides/sulfones
Oxidation of alcohols (in some conditions)
Oxidative cleavage of alkenes to carbonyl compounds (less common)